Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

13. Alcohols and Carbonyl Compounds

Reducing Agent

Organic Chemistry

13. Alcohols and Carbonyl Compounds

Reducing Agent

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2:54 minutes

Problem 36j

Textbook Question

Draw the organic products you would expect to isolate from the following reactions (after hydrolysis).
(j)

Verified step by step guidance

Step 1: Analyze the reactants. The molecule contains two carbonyl groups: a ketone group in the cyclohexane ring and an ester group in the side chain. Sodium borohydride (NaBH₄) is a reducing agent that selectively reduces ketones and aldehydes to alcohols but does not typically reduce esters under standard conditions.

Step 2: Predict the reduction of the ketone group. NaBH₄ will reduce the ketone group in the cyclohexane ring to a secondary alcohol. This involves the addition of a hydride ion (H⁻) to the carbonyl carbon, followed by protonation during hydrolysis.

Step 3: Consider the ester group. Since NaBH₄ does not reduce esters under standard conditions, the ester group will remain unchanged in the product.

Step 4: Hydrolysis step. After the reduction, hydrolysis ensures that any intermediate formed during the reaction is stabilized, and the alcohol group is fully formed.

Step 5: Draw the final product. The cyclohexane ring will now have a secondary alcohol group where the ketone was, while the ester group remains intact. The structure will include a hydroxyl group (-OH) on the cyclohexane ring and the unchanged ester group in the side chain.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Hydrolysis

Hydrolysis is a chemical reaction involving the breaking of a bond in a molecule using water. In organic chemistry, it often refers to the conversion of esters, amides, or other functional groups into their corresponding acids and alcohols or amines. Understanding hydrolysis is crucial for predicting the products of reactions, especially when water is involved in the reaction mechanism.

Reaction Mechanisms

A reaction mechanism is a step-by-step description of how a chemical reaction occurs, detailing the bond-breaking and bond-forming processes. In organic chemistry, mechanisms help predict the products of reactions by illustrating the movement of electrons and the formation of intermediates. Familiarity with common mechanisms, such as nucleophilic substitution or elimination, is essential for accurately determining the expected products.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. In organic chemistry, recognizing functional groups such as alcohols, carboxylic acids, and amines is vital for predicting the behavior of compounds during reactions. The nature of the functional groups involved will significantly influence the products formed after hydrolysis.

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Textbook Question

Suggest carbonyl compounds and reducing agents that might be used to form the following alcohols.

(d)

Textbook Question

Show how this 1° alcohol can be made from the following:

(d) a carboxylic acid

Textbook Question

Predict the products you would expect from the reaction of NaBH₄ with the following compounds. You may assume that these reactions take place in methanol as the solvent.

(e)

Textbook Question

Predict the products you would expect from the reaction of LiAlH₄ followed by hydrolysis with the following compounds. You may assume that these reactions take place in methanol as the solvent.

(e)

Textbook Question

Predict the products you would expect from the reaction of LiAlH₄ followed by hydrolysis with the following compounds. You may assume that these reactions take place in methanol as the solvent.

(d)

Textbook Question

Predict the products of the following reactions:

(a)

(b)

Textbook Question

For each synthesis, start with bromocyclohexane and predict the products. Assume that an excess of each reactant is added so that all possible reactions that can happen will happen.

(b)

Textbook Question

Suggest carbonyl compounds and reducing agents that might be used to form the following alcohols.

(e)

(f)

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